CN112723984B - Method for separating m-bromoiodobenzene and o-bromoiodobenzene - Google Patents
Method for separating m-bromoiodobenzene and o-bromoiodobenzene Download PDFInfo
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- CN112723984B CN112723984B CN202110049913.2A CN202110049913A CN112723984B CN 112723984 B CN112723984 B CN 112723984B CN 202110049913 A CN202110049913 A CN 202110049913A CN 112723984 B CN112723984 B CN 112723984B
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Abstract
The invention provides a method for separating m-bromoiodobenzene and o-bromoiodobenzene, which comprises the following steps: 1) mixing the m-bromoiodobenzene crude product with a solvent to obtain a solution; 2) adding seed crystals of m-bromoiodobenzene into the solution, cooling and crystallizing; 3) and after crystallization, carrying out solid-liquid separation to obtain a solid and a liquid, wherein the solid is the m-bromoiodobenzene. The method leads the m-bromoiodobenzene to rapidly nucleate and crystallize by introducing the specially-made m-bromoiodobenzene seed crystal, avoids the conversion of the m-bromoiodobenzene to the o-bromoiodobenzene in the separation process to the maximum extent, realizes the high-efficiency separation of the m-bromoiodobenzene and the o-bromoiodobenzene, has simple and easy operation, avoids using a large amount of toxic and harmful solvents, can realize complete recovery after the solvents are used, and is energy-saving and environment-friendly.
Description
Technical Field
The invention belongs to the field of inorganic chemistry, and particularly relates to a method for separating m-bromoiodobenzene and o-bromoiodobenzene.
Background
The phenanthroimidazole derivative organic photoelectric material is a novel material and has great industrialization potential in the technical field of organic light-emitting diode display. The m-bromoiodobenzene is one of important intermediates for synthesizing the phenanthroimidazole derivative organic photoelectric material. The m-bromoiodobenzene is a light yellow liquid, the melting point of the m-bromoiodobenzene is-9.3 ℃ under normal pressure, the m-bromoiodobenzene is unstable in the air, and metal copper is required to be added as a stabilizer. In the synthesis process of the phenanthroimidazole derivative photoelectric material, m-bromoiodobenzene and aniline are subjected to coupling reaction under the action of an active metal catalyst, so that an intermediate with rigid molecular groups is provided for subsequent steps. The purity of m-bromoiodobenzene has a great influence on the coupling reaction yield and conversion rate.
The m-bromoiodobenzene synthesized by a chemical method contains a small amount of o-bromoiodobenzene. It is known that the coupling reaction activity of o-bromoiodobenzene under the action of a transition metal catalyst is lower than that of m-bromoiodobenzene, so that the purity and yield of the phenanthroimidazole derivative photoelectric material product are reduced if a small amount of o-bromoiodobenzene contained in the m-bromoiodobenzene is not removed, and the application of the phenanthroimidazole derivative photoelectric material in an organic display device is greatly limited.
The prior method adopts a column chromatography means to separate the m-bromoiodobenzene and the o-bromoiodobenzene, and because the polarities of the m-bromoiodobenzene and the o-bromoiodobenzene are close, the method for separating the m-bromoiodobenzene and the o-bromoiodobenzene puts high requirements on the column efficiency of a chromatographic column, and simultaneously, in order to increase the separation degree, a longer chromatographic column is selected and a large amount of toxic and harmful reagents are used as a mobile phase, so the separation cost is high and the environmental protection is not facilitated. Because m-bromoiodobenzene can be gradually converted into o-bromoiodobenzene in a solvent, a rapid separation technology needs to be developed to realize the high-efficiency separation of the two.
The molecular structural formula of the m-bromoiodobenzene is as follows:
the molecular structural formula of the o-bromoiodobenzene is as follows:
disclosure of Invention
In view of the above-mentioned disadvantages of the prior art, the present invention aims to provide a method for separating m-bromoiodobenzene and o-bromoiodobenzene, which solves the problems of the prior art.
To achieve the above objects and other related objects, the present invention is achieved by the following technical solutions.
One of the purposes of the invention is to provide a method for separating m-bromoiodobenzene and o-bromoiodobenzene, which comprises the following steps:
1) mixing the m-bromoiodobenzene crude product with a solvent to obtain a solution;
2) adding m-bromoiodobenzene seed crystals into the solution, cooling and crystallizing;
3) and after crystallization, carrying out solid-liquid separation to obtain a solid and a liquid, wherein the solid is the m-bromoiodobenzene.
Preferably, the mass percentage of o-bromoiodobenzene in the crude m-bromoiodobenzene is less than 5%. The method for separating o-bromoiodobenzene from m-bromoiodobenzene is more suitable for separating trace o-bromoiodobenzene from trace o-bromoiodobenzene.
Preferably, the solvent is one of methanol, ethanol, acetone and tetrahydrofuran.
Preferably, the mass volume ratio of the m-bromoiodobenzene crude product to the solvent is 1g (5-10) ml.
More preferably, the mass volume ratio of the m-bromoiodobenzene crude product to the solvent is 1g (5-7) ml.
Preferably, in step 2), the preparation method of the m-bromoiodobenzene seed crystal comprises: dropping organic solvent into the m-bromoiodobenzene, and cooling to-15-10 deg.C to form m-bromoiodobenzene seed crystal.
More preferably, the organic solvent is one of methanol, ethanol, acetone and tetrahydrofuran, and the mass ratio of the organic solvent to m-bromoiodobenzene is (0.1-10): (90-99.9).
Further preferably, the mass ratio of the organic solvent to the m-bromoiodobenzene is (1-2): (98-99).
Preferably, in the step 2), the mass ratio of the m-bromoiodobenzene seed crystal to the m-bromoiodobenzene crude product is 1: (30-50).
More preferably, the mass ratio of the m-bromoiodobenzene seed crystal to the m-bromoiodobenzene crude product is 1: (40-50).
Preferably, in the step 2), the cooling rate is 1 ℃/min to 10 ℃/min, the temperature is reduced to-20 ℃ to-10 ℃, and the temperature is maintained for 0.2h to 0.5h after the temperature is reduced.
More preferably, the cooling rate is 1 ℃/min to 3 ℃/min, the temperature is reduced to minus 15 ℃ to minus 12 ℃, and the temperature is maintained for 0.2h to 0.3h after the temperature is reduced.
Preferably, the liquid is subjected to solvent removal to obtain o-bromoiodobenzene.
More preferably, the removal solvent is recovered and removed by vacuum rotary evaporation, the rotary evaporation temperature is 20-50 ℃, the vacuum degree is (-50-0) KPa, the rotary evaporation time is 0.2-0.5 h, and the rotation speed is 50-60 r/min.
Further preferably, the rotary evaporation temperature is 25-45 ℃, the vacuum degree is (-10-0) KPa, the rotary evaporation time is 0.3-0.5 h, and the rotation speed is 55-60 r/min.
The method utilizes the free organic solvent wrapped in the m-bromoiodobenzene crystal to form the seed crystal with a shell-core structure, when the m-bromoiodobenzene seed crystal is changed from the external environment, pressure difference exists between the inside and the outside of the seed crystal to cause volume change of the seed crystal, and stress difference, instantaneous high concentration difference and temperature difference are formed on the solid-liquid boundary layer of the seed crystal and the external solution, so that viscous resistance of the solution is overcome, the m-bromoiodobenzene in the solution is pushed to the solid-liquid boundary layer to quickly form nuclear crystals, and the aim of quickly crystallizing and separating the m-bromoiodobenzene from the solution is fulfilled. Such separation methods have not been reported in the literature known so far. The method disclosed by the patent is very attractive to the field of preparation of high-purity and high-efficiency phenanthroimidazole derivative organic photoelectric materials by using m-bromoiodobenzene.
Compared with the prior art, the invention has the following beneficial effects:
1. the method introduces the m-bromoiodobenzene seed crystal containing the organic solvent, leads the m-bromoiodobenzene to be quickly nucleated and crystallized through induced extrusion, avoids the conversion of the m-bromoiodobenzene to the o-bromoiodobenzene in the separation process to the maximum extent, realizes the high-efficiency separation of the m-bromoiodobenzene and the o-bromoiodobenzene, and has simple and easy operation.
2. The invention avoids using a large amount of toxic and harmful solvents, can realize complete recovery after the solvents are used, and is energy-saving and environment-friendly.
3. The invention adopts the technology of introducing m-bromoiodobenzene crystal seed reverse recrystallization, the purity of the purified m-bromoiodobenzene can reach 99 percent, and the utilization rate of the raw materials is high.
Detailed Description
The following description of the embodiments of the present invention is provided for illustrative purposes, and other advantages and effects of the present invention will become apparent to those skilled in the art from the present disclosure.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention. Test methods in which specific conditions are not specified in the following examples are generally carried out under conventional conditions or under conditions recommended by the respective manufacturers.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those described in the examples may be used in the practice of the invention in addition to the specific methods, devices, and materials used in the examples, in keeping with the knowledge of one skilled in the art and with the description of the invention.
Example 1
In this embodiment, the method for separating m-bromoiodobenzene and o-bromoiodobenzene includes the following steps:
1) adding 50g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 250ml of methanol until the crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 1 wt%.
2) Adding 1.6g of m-bromoiodobenzene seed crystal into the solution in the step 1), cooling to-15 ℃ at the speed of 1 ℃/min, and maintaining for 0.2h after cooling to ensure that the crystals are fully separated out; the preparation process of the m-bromoiodobenzene seed crystal comprises the following steps: in a spherical container, dropwise adding methanol into m-bromoiodobenzene, and then cooling to-20 ℃ to form m-bromoiodobenzene crystals, wherein the mass ratio of methanol to m-bromoiodobenzene is 1: 999.
3) after crystallization, vacuum filtration is carried out to obtain solid and liquid, wherein the solid is the m-bromoiodobenzene, the weight of the solid is 50.8, and the purity of the solid is 99%.
4) And (3) carrying out vacuum rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 20 ℃, the vacuum degree of 0KPa, the rotary evaporation time of 0.2h and the rotation speed of 50r/min to recover methanol, so as to obtain 0.45g of o-bromoiodobenzene and the purity of 99%.
Example 2
In this embodiment, the method for separating m-bromoiodobenzene and o-bromoiodobenzene includes the following steps:
1) adding 50g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 400ml of methanol until the crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 2 wt%.
2) Adding 1.3g of m-bromoiodobenzene seed crystal into the solution in the step 1), cooling to-12 ℃ at the speed of 5 ℃/min, and maintaining for 0.2h after cooling to ensure that the crystallization is fully separated out; the preparation process of the m-bromoiodobenzene seed crystal comprises the following steps: in a spherical container, methanol is dripped into m-bromoiodobenzene, and then the temperature is reduced to-12 ℃ to form m-bromoiodobenzene crystals, wherein the mass ratio of the methanol to the o-bromoiodobenzene is 1: 200.
3) After crystallization, vacuum filtration is carried out to obtain solid and liquid, wherein the solid is the m-bromoiodobenzene, the weight of which is 50g, and the purity of which is 99%.
4) And (3) carrying out vacuum rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 30 ℃, the vacuum degree of-20 KPa, the rotary evaporation time of 0.4h and the rotation speed of 55r/min to recover methanol, thereby obtaining 0.95g of o-bromoiodobenzene and the purity of 99%.
Example 3
In this embodiment, the method for separating m-bromoiodobenzene and o-bromoiodobenzene includes the following steps:
1) adding 50g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 500ml of methanol until the crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 4 wt%.
2) Adding 5.5g of m-bromoiodobenzene seed crystal into the solution in the step 1), cooling to-10 ℃ at the speed of 10 ℃/min, and maintaining for 0.5h after cooling to ensure that the crystallization is fully separated out; the preparation process of the m-bromoiodobenzene seed crystal comprises the following steps: in a spherical container, dropwise adding methanol into m-bromoiodobenzene, and then cooling to-10 ℃ to form crystals of the m-bromoiodobenzene, wherein the mass ratio of the methanol to the m-bromoiodobenzene is 1: 9.
3) after crystallization, vacuum filtration is carried out to obtain solid and liquid, wherein the solid is the m-bromoiodobenzene, the weight of the solid is 53.2g, and the purity is 99%.
4) And (3) carrying out vacuum rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 40 ℃, the vacuum degree of-50 KPa, the rotary evaporation time of 0.2h and the rotation speed of 50r/min to recover methanol, so as to obtain 1.9g of o-bromoiodobenzene and the purity of 99%.
Example 4
In this embodiment, the method for separating m-bromoiodobenzene and o-bromoiodobenzene includes the following steps:
1) adding 10g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 60ml of ethanol until the crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 3 wt%.
2) Adding 0.28g of m-bromoiodobenzene seed crystal into the solution obtained in the step 1), cooling to-13 ℃ at the speed of 3 ℃/min, and maintaining for 0.2h after cooling to ensure that the crystals are fully separated out; the preparation process of the m-bromoiodobenzene seed crystal comprises the following steps: in a spherical container, dropwise adding ethanol into m-bromoiodobenzene, and then cooling to-13 ℃ to form m-bromoiodobenzene crystals, wherein the mass ratio of the ethanol to the m-bromoiodobenzene is 1: 50.
3) after crystallization, vacuum filtration is carried out to obtain solid and liquid, wherein the solid is the m-bromoiodobenzene, the weight of the solid is 9.9g, and the purity is 99%.
4) And (3) carrying out vacuum rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 45 ℃, the vacuum degree of-30 KPa, the rotary evaporation time of 0.4h and the rotation speed of 55r/min to recover ethanol, so as to obtain 0.3g of o-bromoiodobenzene with the purity of 99%.
Example 5
In this embodiment, the method for separating m-bromoiodobenzene and o-bromoiodobenzene includes the following steps:
1) adding 10g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 100ml of acetone until the crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 4 wt%.
2) Adding 0.2g of m-bromoiodobenzene seed crystal into the solution obtained in the step 1), cooling to-14 ℃ at the speed of 5 ℃/min, and maintaining for 0.3h after cooling to ensure that the crystals are fully separated out; the preparation process of the m-bromoiodobenzene seed crystal comprises the following steps: in a spherical container, dropwise adding acetone into m-bromoiodobenzene, and then cooling to-15 ℃ to form m-bromoiodobenzene crystals, wherein the mass ratio of the acetone to the m-bromoiodobenzene is 1: 300.
3) after crystallization, vacuum filtration is carried out to obtain solid and liquid, wherein the solid is the m-bromoiodobenzene, the weight of the solid is 9.77g, and the purity is 99%.
4) And (3) performing rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 40 ℃, the vacuum degree of 0KPa, the rotary evaporation time of 0.3h and the rotation speed of 60r/min to recover acetone to obtain 0.38g of o-bromoiodobenzene with the purity of 99%.
Example 6
In this embodiment, the method for separating m-bromoiodobenzene and o-bromoiodobenzene includes the following steps:
1) adding 10g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 100ml of tetrahydrofuran until the crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 1 wt%.
2) Adding 0.22g of m-bromoiodobenzene seed crystal into the solution obtained in the step 1), cooling to-11 ℃ at the speed of 8 ℃/min, and maintaining for 0.2h after cooling to ensure that the crystals are fully separated out; the preparation process of the m-bromoiodobenzene seed crystal comprises the following steps: in a spherical container, dripping tetrahydrofuran into m-bromoiodobenzene, and then cooling to-11 ℃ to form m-bromoiodobenzene crystals, wherein the mass ratio of the tetrahydrofuran to the m-bromoiodobenzene is 1: 555.
3) after crystallization, vacuum filtration is carried out to obtain solid and liquid, wherein the solid is the m-bromoiodobenzene, the weight of the solid is 10.12g, and the purity is 99%.
4) And (3) carrying out vacuum rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 50 ℃, the vacuum degree of-10 KPa, the rotary evaporation time of 0.5h and the rotation speed of 50r/min to recover tetrahydrofuran to obtain 0.1g of o-bromoiodobenzene with the purity of 99%.
Example 7
In this embodiment, the method for separating m-bromoiodobenzene and o-bromoiodobenzene includes the following steps:
1) adding 10g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 90ml of methanol until the crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 1 wt%.
2) Adding 0.25g of m-bromoiodobenzene seed crystal into the solution obtained in the step 1), cooling to-15 ℃ at the speed of 10 ℃/min, and maintaining for 0.2h after cooling to ensure that the crystals are fully separated out; the preparation process of the m-bromoiodobenzene seed crystal comprises the following steps: in a spherical container, dripping methanol into o-bromoiodobenzene, and then cooling to-15 ℃ to form m-bromoiodobenzene crystals, wherein the mass ratio of the methanol to the m-bromoiodobenzene is 1: 999.
3) after crystallization, vacuum filtration is carried out to obtain solid and liquid, wherein the solid is the m-bromoiodobenzene, the weight of the solid is 10.15g, and the purity is 99%.
4) And (3) carrying out vacuum rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 40 ℃, the vacuum degree of-50 KPa, the rotary evaporation time of 0.4h and the rotation speed of 60r/min to recover methanol, thereby obtaining 0.1g of o-bromoiodobenzene and the purity of 99%.
Comparative example 1
In this comparative example, the process for separating m-bromoiodobenzene and o-bromoiodobenzene comprises the steps of:
1) adding 10g of m-bromoiodobenzene crude product into a reaction bottle, and dropwise adding 50ml of methanol until the m-bromoiodobenzene crude product is completely dissolved to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is 1 wt%.
2) Cooling to-20 deg.C without adding seed crystal, vacuum filtering to obtain solid (9.7 g) and liquid (95% purity).
3) And (3) carrying out vacuum rotary evaporation on the liquid after suction filtration at the rotary evaporation temperature of 40 ℃, the vacuum degree of-25 KPa, the rotary evaporation time of 0.4h and the rotation speed of 60r/min to recover the solvent methanol, thereby obtaining 0.4g of o-bromoiodobenzene and the purity of 99%.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.
Claims (6)
1. A method for separating m-bromoiodobenzene and o-bromoiodobenzene is characterized by comprising the following steps:
1) mixing the m-bromoiodobenzene crude product with a solvent to obtain a solution, wherein the mass percentage of o-bromoiodobenzene in the m-bromoiodobenzene crude product is less than 5%, and the solvent is one of methanol, ethanol, acetone and tetrahydrofuran;
2) adding seed crystals of m-bromoiodobenzene into the solution, cooling and crystallizing;
3) after crystallization, carrying out solid-liquid separation to obtain a solid and a liquid, wherein the solid is the m-bromoiodobenzene;
in the step 2), the preparation method of the m-bromoiodobenzene seed crystal comprises the following steps: dropping an organic solvent into the m-bromoiodobenzene, and then cooling to-15 to-10 ℃ to form seed crystals of the m-bromoiodobenzene, wherein the organic solvent is one of methanol, ethanol, acetone and tetrahydrofuran;
the mass ratio of the seed crystal of the m-bromoiodobenzene to the crude product of the m-bromoiodobenzene is 1 (30-50);
the cooling rate is 1-10 ℃/min, the temperature is reduced to-20 ℃ to-10 ℃, and the temperature is maintained for 0.2-0.5 h after the temperature is reduced.
2. The method for separating m-bromoiodobenzene and o-bromoiodobenzene as claimed in claim 1, wherein the mass volume ratio of the crude m-bromoiodobenzene to the solvent is 1g (5-10) ml.
3. The method for separating m-bromoiodobenzene and o-bromoiodobenzene according to claim 1, wherein the mass ratio of the organic solvent to the m-bromoiodobenzene is (0.1-10): (90-99.9).
4. The method for separating m-bromoiodobenzene and o-bromoiodobenzene as claimed in claim 1, wherein in step 3), the o-bromoiodobenzene is obtained after the solvent is removed from the liquid.
5. The method for separating m-bromoiodobenzene and o-bromoiodobenzene as claimed in claim 4, wherein the removal solvent is recovered and removed by vacuum rotary evaporation.
6. The method for separating m-bromoiodobenzene and o-bromoiodobenzene as claimed in claim 5, wherein the rotary evaporation temperature is 20 ℃ to 50 ℃, the vacuum degree is (-50 to 0) KPa, the rotary evaporation time is 0.2h to 0.5h, and the rotation speed is 50r/min to 60 r/min.
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| WO2011154953A1 (en) * | 2010-06-10 | 2011-12-15 | Technion R&D Foundation Ltd. | Process for the preparation of iodides |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011154953A1 (en) * | 2010-06-10 | 2011-12-15 | Technion R&D Foundation Ltd. | Process for the preparation of iodides |
Non-Patent Citations (3)
| Title |
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| Regiospecific Synthesis of Mono- and Polyiodo Derivatives of Benzene;Felix guy,et al.;《Angew.Chem.Int.Ed.Engl.》;19771231;第16卷(第7期);第488-489页 * |
| 两种溴碘代苯新合成方法的研究;谢政等;《化学试剂》;20041231;第26卷(第2期);第67-69页 * |
| 碘代芳烃的合成研究;许丹红等;《浙江工业大学学报》;20080228;第36卷(第1期);第20-23页 * |
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